Highlands Packages (Flight + Hotel)

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  • Better together

    Save up to ฿4,531 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Where to stay in Highlands

Find the best Highlands areas and neighborhoods for the activities you enjoy most. Learn more about Highlands
Downtown Boston which includes a city and night scenes as well as a small group of people

Downtown Boston

4.5/5(94 area reviews)

The heart of America’s revolutionary history lies in the center of this city. Uncover the story of the nation and enjoy excellent arts and dining venues.

Find hotels in Downtown Boston

Top hotels in Highlands

Harborside Inn Of Boston

Harborside Inn Of Boston

4 out of 5
185 State St Boston MA
9.2/10 Wonderful! (6,144 reviews)
The staff was so nice and the check-in was easy. It was a nicely decorated boutique hotel that I would definitely stay in again. It was close to absolutely everything; the Freedom Trail, North End, Harbor, Boston Common, and there was a subway station immediately outside of the hotel. The only downside ...

Reviewed on 14 Jan 2026

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Harborside Inn Of Boston
Encore Boston Harbor

Encore Boston Harbor

5 out of 5
1 Broadway Everett MA
Fully refundableReserve now, pay when you stay
The price is ฿7,532 per night from 9 Feb to 10 Feb
฿7,532
฿8,413 total
9 Feb - 10 Feb
includes taxes & fees
9.6/10 Exceptional! (3,507 reviews)
Room was spacious, spotless and comfortable.

Reviewed on 11 Jan 2026

Encore Boston Harbor
Hilton Boston Back Bay

Hilton Boston Back Bay

4 out of 5
40 Dalton St Boston MA
Fully refundableReserve now, pay when you stay
The price is ฿3,696 per night from 18 Jan to 19 Jan
฿3,696
฿5,246 total
18 Jan - 19 Jan
includes taxes & fees
8.4/10 Very Good! (1,251 reviews)
Check in was great. I'm tall, so I struggle with looking down at name tags. It feels awkward, especially if someone presents as female, I am a male. My check in attendant was helpful, kind, and knowledgeable. I appreciate them, but I didn't catch their name. Maybe at check there could be a nameplate? ...

Reviewed on 12 Jan 2026

Hilton Boston Back Bay
See all 3,588 properties in Highlands
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much does a Highlands holiday package cost?
From as low as , you can tailor your Highlands holiday package. Simply combine hotels, flights and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Highlands?
Combine your hotels and flights, add extras such as tours, and save with a Highlands holiday package. You won't just walk away with superb discounts on your escape — you'll have plenty of choice within your reach too. When you book with Expedia, you'll have your pick of over 550 partner airlines and 1,000,000 properties throughout the world. Your affordable holiday begins right here, right now!
Where should I stay in Highlands?
Stay at a hotel near Bentley College. This impressive sight is in the middle of the action and on the must-see lists of many tourists.
How far in advance should I book my Highlands holiday?
Browse Expedia to compare international flights as early as possible. In many cases, you can purchase a seat up to 12 months in advance. If you can't see your preferred carrier, or you've left things to the last minute, don't worry. Cheap fares to Highlands occasionally appear a few weeks before the date of departure.
What does an Expedia Highlands travel package include?
Packages include rental cars, hotels and flights, but you can combine any of them to create your ideal Highlands getaway. You can also add on some activities and experiences once you've made your booking. You're the boss! When you bundle your bookings with Expedia, you'll enjoy deals you won't find elsewhere.
What should I know before booking a Highlands travel package?
You'll score big savings when you bundle your hotels, flights and rental cars into a travel package. Not only that, booking everything together makes trip planning much easier. So why waste your money or time? Whether you're organising a fancy romantic getaway or an affordable family break, check out our holiday packages today.
Can I choose my airline with a Highlands Expedia holiday package?
With a holiday package, you're in control. Whether you'd prefer to fly to Highlands in economy or business class, simply select from the available airline options. Expedia has access to more than 550 partner airlines globally.
If I'm not able to travel, can I cancel my Highlands holiday package?
If your holiday plans in Highlands have changed, it's a relief to know that it's possible to cancel your booking. If your booking was made in the last 24 hours, you may be eligible to receive a refund. If your booking was made more than 24 hours ago, your airline, hotel or car rental company may impose fees. To find out more, visit our Customer Service Portal.

Popular places to visit

Fenway Park which includes a sporting event and night scenes as well as a large group of people

Fenway Park

Catch a game or take a tour at one of America’s most historic and beloved ballparks.

Fenway Park
Boston Common which includes a skyscraper, landscape views and a park

Boston Common

The oldest public park in the United States has been the stage for centuries of drama. These days it’s the perfect place to unwind.

Boston Common
Harvard University showing a city and heritage architecture

Harvard University

Walk in the footsteps of presidents and Nobel laureates at one of the oldest and most prestigious universities in the United States.

Harvard University

Things to do

Step into a festive winter oasis at Stratus bar this holiday season! Adorned with glittering icicles, sparkling lights, and festive winter elements, this experience is a must must-visit.

View Boston Observation Deck Admission Tickets

฿1,070
per adult
88% of travellers recommend
View Boston Observation Deck Admission Tickets
LEGO Discovery Center Boston Admission Ticket

LEGO Discovery Center Boston Admission Ticket

฿882
per adult
100% of travellers recommend
LEGO Discovery Center Boston Admission Ticket
Go City: Boston All-Inclusive Pass with 45+ Attractions

Go City: Boston All-Inclusive Pass with 45+ Attractions

฿2,642
per adult
80% of travellers recommend
Go City: Boston All-Inclusive Pass with 45+ Attractions
See all activities in Boston
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.